Plot: While in his honeymoon in a paradisaical beach, the conservative risk analyst of an insurance company Reuben Feffer finds his wife Lisa Kramer having intercourse with her scuba instructor Claude in his boat. Reuben immediately returns to New York and his friend Sandy Lyle invites him to go to a party. There he meets his former high school friend Polly Prince, who is a very independent woman that lives in the edge with her blind ferret in a cozy but simple apartment. Although having very different behaviors, they date and fell a great attraction for each other. When Lisa returns, Reuben has to decide if he wants to live his life in the suburb with his unfaithful wife, or have a risky relationship with Polly.
Alternative Plot: Actuary Reuben Feffer (Ben Stiller) is so aware of the risks inherent in all situations that he is unable to risk anything. His bride, Lisa Kramer (Debra Messing), seems perfect but cheats on him during their honeymoon. Back home in New York City, his best friend, former child star Sandy (Philip Seymour Hoffman), urges him to attend a party. There he meets an ex-classmate, Polly Prince (Jennifer Aniston), whose spirited ways spark his adoration but confound his neuroses.
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